"This Used to Be My Playground" is a song recorded by American singer Madonna. It is the theme for the film A League of Their Own, which starred Madonna, and portrayed a fictionalized account of the real-life All-American Girls Professional Baseball League. Madonna was asked to record a song for the film's soundtrack. At that time she was busy recording her fifth studio album, Erotica, with producer Shep Pettibone. They worked on some ideas and came up with "This Used to Be My Playground" in two days. Once presented to director Penny Marshall's team, the song was released as a standalone single on June 16, 1992, by Warner Bros. Records. However, it was not available on the film's soundtrack due to contractual obligations and was later added to the Olympics-inspired Barcelona Gold compilation album, released that summer. The song was included on Madonna's 1995 ballads compilation Something to Remember.

Written and produced by Madonna and Pettibone, "This Used to Be My Playground" was the first time that Pettibone worked with live string arrangement. Madonna recorded the song on a Shure SM57 microphone, with instrumentation from piano, organ, strings and a basic drum sounds. During the final recording, the duo had to redo the whole orchestra section to tailor it for the song. "This Used to Be My Playground" starts with a keyboard introduction and strings, with Madonna singing in expressive but subdued vocals. Its verse and chorus merge into each other for having a continuity in the song, but the track ends abruptly. Lyrically it discusses visiting one's childhood places and not letting go of the past.

The song received positive reviews from critics, who noted it as an essential addition in Madonna's repertoire. The song earned the singer a Golden Globe Award nomination for Best Original Song. It was a commercial success, reaching the top of the charts on the US Billboard Hot 100; the track was Madonna's tenth chart-topping single, breaking her tie with Whitney Houston to become the female artist with the most number one singles at that time. It also reached the top of the charts in Canada, Finland, Italy and Sweden, while reaching the top-ten of the charts in Australia, Belgium, France, Germany, Ireland, Netherlands, Norway, Spain, Switzerland and the United Kingdom. Even though the song was commercially successful, Madonna has never performed it in any of her concert tours, nor included it on her greatest hits albums, GHV2 (2001) and Celebration (2009).

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